FIGURE 5.24 Alkylation of cysteine residues by busulfan.

of brain tumors, which led to the synthesis of a large number of nitrosoureas, including lomustine (CCNU) and its methyl derivative semustine, carmustine (BCNU), nimustine (ACNU), the water-soluble tauromustine and fotemustine, but toxicity problems have prevented their widespread use. In 1967, streptozoto-cin (streptozocin), a hydrophilic natural nitrosourea, was isolated from a strain of S. achromogenes. This compound was chosen as a lead because initial SAR studies suggested that hydrophilic nitrosoureas were more potent and less toxic, and a number of analogs, like chlorozotocin, were prepared. Currently, the most clinically important nitrosoureas are CCNU, BCNU, ACNU, and streptozotocin.


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